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Details for Patent: RE39265

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Details for Patent: RE39265

Title:Heteroarylpiperidines, and their use as antipsychotics and analgetics
Abstract: Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. The compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.
Inventor(s): Strupczewski; Joseph T. (Flemington, NJ), Bordeau; Kenneth J. (Kintnersville, PA), Glamkowski; Edward J. (Warren, NJ), Chiang; Yulin (Convent Station, NJ), Helsley; Grover C. (Stockton, NJ)
Assignee: Aventis Pharmaceuticals Inc. (Bridgewater, NJ)
Filing Date:Nov 09, 2000
Application Number:09/708,475
Claims:1. A compound of the formula: ##STR00166## wherein, X is --O--, --S--, --NH--, .[.--N(R.sub.2).]. .Iadd.or ##STR00167## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C 10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is as defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino.Iaddend..Iadd., when p is 1; Y is lower alkoxy when p is 2 and X is --O--.Iaddend.; .[.R.sub.1 is R.sub.20 R.sub.21 or R.sub.22, wherein: R.sub.20 is --(CH.sub.2).sub.5, where.]. n is 2, 3, 4, or 5; .[.R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.CH.sub.2--, the --CH--CH-- bond being cis or trans; R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1-C.sub.6 linear alkyl group, phenyl group, or ##STR00168## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NO.sub.2, or halogen, p is as previously defined;.]. R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono a dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, .[.monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl,.]. --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, .Iadd.or .Iaddend. --CH(OR.sub.7)-alkyl,.Iadd.;.Iaddend. .[.--C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl;.]. .Iadd.wherein.Iaddend. alkyl is lower alkyl; aryl is phenyl or ##STR00169## where.Iadd.in .Iaddend.R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano, trifluoromethyl, or trifluoromethoxy; heteroaryl is ##STR00170## Q.sub.3 is --O--, --S--, --NH--, .Iadd.or .Iaddend.--CH.dbd.N--; .[.W is CH.sub.2 or CHR.sub.8 or N--R.sub.9;.]. R.sub.7 is hydrogen, lower alkyl, or .[.alkanoyl.]. ; .Iadd.lower alkyl--(C.dbd.O)--.Iaddend.; .[.R.sub.8 is lower alkyl; R.sub.9 is hydroxy, alkoxy, or --NRF.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl or --C(.dbd.O)-heteroaryl, where aryl and heteroaryl are as defined above;.]. and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, .[.C.sub.1=14 C.sub.4.]. .Iadd.C.sub.1-C.sub.4 .Iaddend.alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is .Iadd.H or .Iaddend.C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, .[.R.sub.1 is R.sub.20,.]. R is H, and m=1; .[.all geometric, optical, and stereoisomers thereof,.]. or a pharmaceutically acceptable acid addition salt thereof.

2. A compound as claimed in claim 1, wherein X is --O--, --S--, .Iadd.or .Iaddend.--NH--.

3. A compound as claimed in claim 1, wherein Y is hydrogen, chlorine, bromine, or fluorine.

4. A compound as claimed in claim 1, wherein n is 2, 3, or 4.

5. A compound as claimed in claim 1, wherein X is --O --.

6. A compound as claimed in claim 1, wherein X is --S--.

7. A compound as claimed in claim 1, wherein X is --NH--.

8. A compound as claimed is claim 1, wherein X is ##STR00171##

9. A compound as claimed in claim 1, wherein X is --O--, --S--, or --NH--; Y is H, Cl, F, .Iadd.or .Iaddend.CF.sub.3; R is selected from the group consisting of hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, --OH, Cl, F, Br, I .[.acyl,.]. C.sub.1-C.sub.3 monoalkylamino, acylamino, .[.--NO.sub.2--,.]. --NO.sub.2, OCF.sub.3, .Iadd.and .Iaddend.--CF.sub.3; and n is 2, 3, or 4.

10. A compound as claimed in claim 9, wherein the substituent Y is in the 5- or 5-position.

11. A compound as claimed in claim 10, wherein m is 2.

12. A compound as claimed in claim 10, wherein n is 3.

13. A compound as claimed is claim 10, wherein p is 1.

14. A compound as claimed in claim 1, which is 1-[4-[3-[4-(1H-indazol-3-yl)-1-piperazinyl]propoxy]-3-methoxyphenyl]ethan- one or a pharmaceutically acceptable acid addition salt thereof.

15. A compound as claimed in claim 1, which is 1-[4-[4-[4-(1H-indazol-3-yl)-1-piperazinyl]butoxy[-3-methoxyphenyl]ethano- ne fumarate or a pharmaceutically acceptable acid addition salt thereof.

16. A compound as claimed in claim 1, which is 1-[4-(3-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]propoxy]-3-methoxyphe- nyl]ethanone or it pharmaceutically acceptable acid addition salt thereof.

17. A compound as claimed in claim 1, which is 1-[4-[4-[4-(6-fluoro-1H-indazol-3-yl)-1-piperazinyl]butoxy]-3-methox.Iadd- .y.Iaddend.phenyl]ethanone or a pharmaceutically acceptable acid addition salt thereof.

18. A compound as claimed in claim 1, which is 1-[4-[3-[4-(6-chloro-1H-indazol-3-yl)-1-piperazinyl]propoxy]-3-methox.Iad- d.y.Iaddend.phenyl]ethanone or a pharmaceutically acceptable acid addition salt thereof.

19. A compound as claimed in claim 1, which is 1-[4-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butoxy]-3-methoxypheny- l]ethanone or a pharmaceutically acceptable acid addition salt thereof.

20. A compound as claimed in claim 1, which is 1-[4-[3-[4-(1-benzoyl-6-fluoro-1H-indazol-3-yl)-1-piperazinyl]-propoxy]-3- -methoxyphenyl]ethanone sesquifumarate or a pharmaceutically acceptable acid addition salt thereof.

21. A compound as claimed in claim 1, which is 1-[4-[4-[4-(6-chloro-1H-indazol-3-yl)-1-piperazinyl]butoxy]-3-methoxyphen- yl]ethanone or a pharmaceutically acceptable acid addition salt thereof.

22. A compound as claimed in claim 1, which is 1-[4-[3-[4-(1,2-benzisothiazol-3 yl)-1-piperazinyl]propoxy]-3-methoxyphenyl]ethanone hemifumarate or a pharmaceutically acceptable acid addition salt thereof.

23. A compound as claimed in claim 1, which is 1-[4-[2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethoxy)-3-methoxypheny- l]ethanone or a pharmaceutically acceptable acid addition salt thereof.

24. A compound as claimed in claim 1, which is 1-[4-[2-[4-(6-chloro-1H-indazol-3-yl)-1 piperazinyl]ethoxy]-3-methoxyphenyl]ethanone or a pharmaceutically acceptable acid addition salt thereof.

25. A compound of the formula: ##STR00172## wherein X is --O--, --S--, --NH--, or .[.--N--R.sub.2.]. ##STR00173## p is 1 or 2; Y is hydrogen, Cl, Br, or F when p is 1; Y is lower alkoxy .[.or halogen.]. when p is 2 and X is --O--; R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and .[.phenyl sulfonyl.]. .Iadd.phenylsulfonyl .Iaddend.groups; aryl is phenyl or ##STR00174## where.Iadd.in .Iaddend.R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano, trifluoromethyl, or trifluoromethoxy; n is 2, 3, or 4; R is hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, hydroxyl, .[.acyl, (C.sub.2-C.sub.11) alkanoyl,.]. Cl, F, Br, I, amino, C.sub.1-C.sub.3 mono- or dialkylamino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, --C(.dbd.O)-alkyl, or --CH(OR.sub.7)-alkyl alkyl is lower alkyl; R.sub.7 is hydrogen, lower alkyl, or aryl; and m is 1, 2, or 3; .Iadd.with the exclusion of compounds wherein X is --O-- or --S--, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.3 alkyl, chlorine, fluorine, bromine, iodine, or C.sub.1-C.sub.3 alkoxy; with the exclusion of compounds wherein X is --S--, R is H, and m=1;.Iaddend. or a pharmaceutically acceptable acid addition salt thereof.

26. A compound of the formula; ##STR00175## wherein X is --O-- p is 1 or 2; Y is hydrogen, hydroxy, Cl, Br, or F, when p is 1; Y is lower alkoxy.[., hydroxy, or halogen.]. when p is 2; n is 2, 3, or 4; R is hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, hydroxyl, .[.acyl, (C.sub.2-C.sub.11) alkanoyl,.]. Cl, F, Br, I, amino, C.sub.1-C.sub.3 mono- or dialkylamino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, --C(.dbd.O)--alkyl, or --CH(OR.sub.7)--alkyl .[.,.]. ; alkyl is lower alkyl; R.sub.7 is hydrogen, lower alkyl, or acyl; and m is 1, 2, or 3; .Iadd.with the exclusion of compounds wherein Y is hydrogen, C.sub.1-C.sub.3 alkyl, chlorine, fluorine, bromine, iodine, or C.sub.1-C.sub.3 alkoxy;.Iaddend. or a pharmaceutically acceptable acid addition salt thereof.

27. A compound of the formula: ##STR00176## wherein X is --S--; p is 1.[.or 2.]. ; Y is hydrogen. Cl, Br, or F.[., when p is 1.]. ; .[.Y is lower alkoxy or halogen when p is 2;.]. n is 2, 3, or 4; R is hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, hydroxyl, .[.acyl, (C.sub.2-C.sub.11) alkanoyl, .]. Cl, F, Br, I, amino, C.sub.1-C.sub.3 mono- or dialkylamino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, --C(.dbd.O)--alkyl, or --CH(OR.sub.7)--alkyl.[.,.]. .Iadd.;.Iaddend. alkyl is lower alkyl; R.sub.7 is hydrogen, lower alkyl, or aryl; and m is 1, 2, or 3; .Iadd.with the exclusion of compounds wherein Y is hydrogen and R is hydrogen, C.sub.1-C.sub.3 alkyl, chlorine, fluorine, bromine, iodine, or C.sub.1-C.sub.3 alkoxy; with the exclusion of compounds wherein R is H, and m=1;.Iaddend. or a pharmaceutically acceptable acid addition salt thereof.

28. A compound of the formula: ##STR00177## wherein X is --NH--; p is 1.[.or 2.]. ; Y is hydrogen, Cl, Br, or F.[., when p is 2;.]. .[.Y is lower alkoxy or halogen when p is 2;.]. n is 2, 3, or 4; R is hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, hydroxyl, .[.acyl, (C.sub.2-C.sub.11) alkanoyl,.]. Cl, F, Br, I, amino, C.sub.1-C.sub.3 mono- or dialkylamino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, --C(.dbd.O)--alkyl, or --CH(OR.sub.7)--alkyl.[.,.]. .Iadd.;.Iaddend. alkyl is lower alkyl; R.sub.7 is hydrogen, lower alkyl, or acyl; and m is 1, 2, or 3; or a pharmaceutically acceptable acid addition salt thereof.

29. A compound of the formula: ##STR00178## wherein X is ##STR00179## p is 1 .[.or 2.]. ; Y is hydrogen, Cl, Br, or F.[., when p is 1.]. ; .[.Y is lower alkoxy or halogen when p is 2.]. ; R.sub.2 is selected from the group consisting of lower alkyl, aryl, lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) .[.aroyl,.]. alkanoyl, and phenylsulfonyl groups; aryl is phenyl or ##STR00180## where.Iadd.in .Iaddend.R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano, trifluoromethyl, or trifluoromethoxy; n is 2, 3, or 4; R is hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, hydroxyl, .[.acyl, (C.sub.2-C.sub.11) alkanoyl,.]. Cl, F, Br, I, amino, C.sub.1-C.sub.3 mono- or dialkylamino, acylamino, --NO.sub.2, --OCF.sub.3, --CF.sub.3, --C(.dbd.O)-alkyl, or --CH(OR.sub.7)-alkyl.[.,.]. .Iadd.;.Iaddend. alkyl is lower alkyl; R.sub.7 is hydrogen, lower alkyl, or acyl; and m is 1, 2, or 3; or a pharmaceutically acceptable acid addition salt thereof.

30. A pharmaceutical composition, which comprises a compound of the formula: ##STR00181## wherein X is --O--, --S--, or ##STR00182## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; where.Iadd.in .Iaddend.aryl is .Iadd.as .Iaddend.defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino.Iadd., when p is 1; Y is lower alkoxy when p is 2 and X is --O--;.Iaddend. .[.R.sub.1 is R.sub.20, R.sub.21 or R.sub.22, wherein: R.sub.20 is --CH.sub.2).sub.n-- where.]. n is 2, 3, 4, or 5; .[.R.sub.21 is --CH.sub.2--CH--CH.sub.2--, --CH.sub.2--C.dbd.CH--CH.sub.2--, --CH.sub.2--CH.dbd.CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R.sub.22 1iS R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least on C.sub.1-C.sub.6 linear alkyl group, phenyl group, or ##STR00183## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen, and p as previously defined;.]. R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, .[.monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl,.]. --C(.dbd.O)--alkyl, --C(.dbd.O)--O--alkyl, --C(.dbd.O)--aryl, --C(.dbd.O)--heteroaryl, .Iadd.or.Iaddend.--CH(OR.sub.2)--alkyl.[.,.]. .Iadd.;.Iaddend. .[.--C(.dbd.W)--alkyl, --C(.dbd.W)--aryl, or --C(.dbd.W)--heteroaryl;.]. alkyl is lower alkyl; aryl is phenyl or ##STR00184## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano, trifluoromethyl, or trifluoromethoxy; heteroaryl is ##STR00185## Q.sub.3 is --O--, --S--, NH--, .Iadd.or .Iaddend.--CH.dbd.K--; .[.W is CH.sub.2 or CHR.sub.8, or --N.dbd.R.sub.9;.]. R.sub.7 is hydrogen, lower alkyl, or .[.(C.sub.2-C.sub.11) alkanoyl.]. .Iadd.lower alkyl--(C.dbd.O)--.Iaddend., .[.R.sub.8 is lower alkyl; R.sub.9 is hydroxy, alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)--aryl or --C(.dbd.O)--heteroaryl, where aryl and heteroaryl are as defined above;.]. and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is .Iadd.H or .Iaddend.C.sub.1-C.sub.3 alkyl; with the exclusion of compounds wherein X is --S--, .[.R.sub.1 is R.sub.20,.]. R is H, and m=1; .[.all geometric, optical, and stereoisomers thereof,.]. or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier therefor.

31. An antipsychotic composition, which comprises a compound of the formula: ##STR00186## wherein X is --O--, --S--, --NH--, or ##STR00187## R.sub.1 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; where.Iadd.in .Iaddend.aryl is .Iadd.as .Iaddend.defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino.Iadd., when p is 1.Iaddend.; .Iadd.Y is lower alkoxy when p is 2 and X is --O--;.Iaddend. .[.R.sub.1 is R.sub.20, R.sub.21 or R.sub.22, wherein: R.sub.20 is --(CH.sub.2).sub.n-- where.]. n is 2, 3, 4, or 5; .[.R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least on C.sub.1-C.sub.6 linear alkyl group, phenyl group, or ##STR00188## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen, a p is as previously defined;.]. R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, .[.monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl,.]. --C(.dbd.O)--aryl, --C(.dbd.O)--O--alkyl, --C(.dbd.O)--aryl, --C(.dbd.O)--heteroaryl, .Iadd.or.Iaddend. --CH(OR.sub.7)--alkyl.[.,.]. .Iadd.;.Iaddend. .[.--C(.dbd.W)--alkyl, --C(.dbd.W)--aryl, or --C(.dbd.W)--heteroaryl;.]. alkyl is lower alkyl; aryl is phenyl or ##STR00189## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00190## Q.sub.3 is --O--, --S--, --NH--, .Iadd.or .Iaddend.--CH.dbd.N--; .[.W is CH.sub.2 or CH.sub.8 or N--R.sub.9;.]. R.sub.7 is hydrogen, lower alkyl, or .[.(C.sub.2-C.sub.11) alkanoyl.]. .Iadd.lower alkyl--(C.dbd.O)--.Iaddend.; .[.R.sub.8 is lower alkyl; R.sub.9 is hydroxy, alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)--aryl or C(.dbd.O)--heteroaryl, where aryl and heteroaryl are as defined above;.]. and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is .Iadd.H or .Iaddend.C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, .[.R.sub.1 is R.sub.20,.]. R is H, and m=1; .[.all geometric, optical, and stereoisomers thereof,.]. or a pharmaceutically acceptable acid addition salt thereof, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor.

32. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating effective amount of a compound of the formula: ##STR00191## wherein X is --O--, --S--, --NH--, or ##STR00192## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; where aryl is .Iadd.as .Iaddend.defined hereinafter; p is 1 or 2; Y is hydrogen, lower alky, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, .Iadd.when p is 1; Y is lower alkoxy when p is 2 and X is --O--;.Iaddend. .[.R.sub.1 is R.sub.20, R.sub.21 or R.sub.22, wherein: R.sub.20 is --(CH.sub.2).sub.n-- where.]. n is 2, 3, 4, or 5; .[.R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.22 are substitutes by at least on C.sub.1-C.sub.6 linear alkyl group, phenyl group, or ##STR00193## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, NO.sub.2, --NH.sub.2 or halogen, and p is as previously defined;.]. R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, .[.monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl,.]. --(.dbd.O)--alkyl, --C(.dbd.O)--O--alkyl, --C(.dbd.O)--aryl, --C(.dbd.O)--heteroaryl, .Iadd.or.Iaddend. --CH(OR.sub.7)--alkyl.[.,.]. .Iadd.;.Iaddend. .[.--C(.dbd.W)--alkyl, --C(.dbd.W)--aryl, or --C(.dbd.W)--heteroaryl;.]. .Iadd.wherein .Iaddend.alkyl is lower alkyl; aryl is phenyl or ##STR00194## where.Iadd.in .Iaddend.R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano trifluoromethyl, or trifluoromethoxy; heteroaryl is ##STR00195## Q.sub.3 is --O--, --S--, --NH--, .Iadd.or .Iaddend.--CH.dbd.N--; .[.W is CH.sub.2 or CHR.sub.8 or --N--R.sub.9;.]. R.sub.7 is hydrogen, lower alkyl, or .[.(C.sub.2-C.sub.11) alkanoyl;.]. .Iadd.lower alkyl--(C.dbd.O)--.Iaddend.; .[.R.sub.8 is lower alkyl; R.sub.9 is hydroxy, alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)--aryl or --C(.dbd.O)--heteroaryl, where aryl and heteroaryl are as defined above; .]. and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where.Iadd.in .Iaddend.R.sub.23 is .Iadd.H or .Iaddend.C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, .[.R.sub.1 is R.sub.20,.]. R is H, and m=1; .[.all geometric, optical, and stereoisomers thereof,.]. or a pharmaceutically acceptable acid addition salt thereof.

33. An analgesic composition, which comprises a compound of the formula: ##STR00196## wherein, X is --O --, --S--, --NH--, or .[.--N(R.sub.2).]. ##STR00197## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, sad phenylsulfonyl groups; where.Iadd.in .Iaddend.aryl is .Iadd.as .Iaddend.defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or .Iadd.amino, when p is 1;.Iaddend. .Iadd.Y is lower alkoxy when p is 2 and X is --O--;.Iaddend. .[.R.sub.7 is R.sub.20, R.sub.21 or R.sub.22, wherein: R.sub.20 is --(CH.sub.2).sub.n-- where.]. n is 2, 3, 4, or 5; .[.R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R.sub.22 is R.sub.20 or R.sub.21, in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least on C.sub.1-C.sub.6 linear alkyl group, phenyl group, or ##STR00198## where Z.sub.1, lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen, and p is as previously defined;.]. R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono at dialkylamino nitro, lower alkyl, thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, .[.monoalkylaminocarbonyl dialkylaminocarbonyl, formyl,.]. --C(.dbd.O)--alkyl, --C(.dbd.O)--O--alkyl, --C(.dbd.O)--aryl, --C(.dbd.O)--heteroaryl, .Iadd.or.Iaddend. --CH(OR.sub.7)--alkyl.[.,.]. ; .[.--C(.dbd.W)--alkyl, --C(.dbd.W)--aryl, or --C(.dbd.W)--heteroaryl;.]. .Iadd.wherein.Iaddend. alkyl is lower alkyl; aryl is phenyl or ##STR00199## where.Iadd.in .Iaddend.R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, Iodine, lower monoalkylamino, .[.lower dialkylamino,.]. nitro, cyano, trifluoromethyl, or trifluoromethoxy; heteroaryl is ##STR00200## .Iadd.wherein .Iaddend.Q.sub.3 is --O --, --S--, --NH--, .Iadd.or .Iaddend.--CH.dbd.N--; .[.W is CH.sub.2 or CHR.sub.8 or N--R.sub.9;.]. R.sub.7 is hydrogen, lower alkyl, or .[.(C.sub.2-C.sub.11) alkonyl.]. .Iadd.lower alkyl--(C.dbd.O)--.Iaddend.; .[.R.sub.8 is lower alkyl; R.sub.9 is hydroxy, alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)--aryl, or --C(.dbd.O)--heteroaryl, where aryl and heteroaryl arc as defined above;.]. and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen C.sub.1--C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where.Iadd.in R.sub.7 .Iaddend.is .Iadd.H or .Iaddend.C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, .[.R.sub.1 is R.sub.20,.]. m=1; .[.all geometric, optical, and stereoisomers thereof,.]. or a pharmaceutically acceptable acid addition salt thereof, in an amount sufficient to produce a pain-relieving effect and a pharmaceutically acceptable carrier therefor.

34. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of a .[.compound.]. .Iadd.composition .Iaddend.as claimed in claim 33.

35. A pharmaceutical composition, which comprises a compound as claimed in claim 1, 25, 26, 27, 28, or 29, and a pharmaceutically acceptable carrier therefor.

36. An, .[.antispsychotic.]. .Iadd.antipsychotic .Iaddend.composition, which comprises a compound as claimed in claim 1, 25, 26, 27, 28, or 29, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor.

37. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating effective amount of a compound as claimed in claim 1, 25, 26, 27, .[.29.]. .Iadd.28 .Iaddend.or 29.

38. An analgesic composition, which comprises a compound as claimed in claim 1, 25, 26, 27, 28, or 29, in an amount sufficient to producer a pain-relieving effect, and a pharmaceutically acceptable carrier therefor.

39. A method of alleviating pain which comprises administering to a mammal a pain-relieving effective amount of a compound as claimed in 1, 25, 26, 27, 28, or 29.

40. An antipsychotic composition, which comprises a compound as claimed in claim 1, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor.

41. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating effective amount of a compound as claimed in claim 1.

42. An analgesic composition, which comprises a compound as claimed in claim 1, in an amount sufficient to produce a pain-relieving affect and a pharmaceutically acceptable carrier therefor.

43. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of a compound as claimed in 1.

44. The compound of any one of claims 1, 25, 26, 27, 28, and 29, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts of mineral acids, salts of monobasic carboxylic acids, salts of dibasic carboxylic acids, and salts of tribasic carboxylic acids.

45. The compound of claim 44, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts of hydrochloric acid, sulfuric add, nitric acid, acetic acid, propionic acid, maleic acid, fumaric acid, carboxysuccinic acid, an citric acid.

.Iadd.46. A compound of the formula ##STR00201## wherein X is --O--, --S--, --NH--, or ##STR00202## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl(C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) lkanoyl, and phenylsulfonyl groups; aryl is as defined hereinafter; p is 1 or 2: Y hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when p is 2 and X is --O--; (R.sub.1) is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, fluoromethyl, trifluoroacetyl, aminocarbonyl, dialkylaminocarbonyl, formyl --(.dbd.O)-alkyl, --C(.dbd.O)--O--alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; wherein alkyl is lower alkyl; aryl is phenyl or ##STR00203## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy; heteroaryl is ##STR00204## wherein Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)-heteroaryl, wherein aryl and heteroaryl are as defined above; and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4, alkyl, chlorine, fluorine, bromine, iodine cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 wherein R.sub.23 is H or C.sub.1-C.sub.4 alkyl; all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt, thereof..Iaddend.

.Iadd.47. A compound as claimed in claim 46, wherein X is --O--, or --O--, or --NH--..Iaddend.

.Iadd.48. A compound as claimed in claim 46 wherein Y is hydrogen, chlorine , bromine, or fluorine..Iaddend.

.Iadd.49. A compound as claimed in claim 46, wherein X is --O--..Iaddend.

.Iadd.50. A compound as claimed in claim 46, wherein X is --S--..Iaddend.

.Iadd.51. A compound as claimed in claim 46 wherein X is --NH--..Iaddend.

.Iadd.52. A compound as claimed in claim 46 wherein X is ##STR00205## .Iaddend.

.Iadd.53. A compound as claimed in claim 46, wherein X is --O--, --S--, or --NH--; Y is H, Cl, F, or --CF.sub.3; R is from the group consisting of hydrogen, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, --OH, Cl, F, Br, C.sub.1-C.sub.3 monoalkylamino, acylamino, --NO.sub.2, --OCF.sub.3, and --CF.sub.3..Iaddend.

.Iadd.54. A compound as claimed in claim 53, wherein the substituent X is in the 5- or 6-position..Iaddend.

.Iadd.55. A compound as claimed in claim 54, wherein m is 2..Iaddend.

.Iadd.56. A compound as claimed in claim 54, wherein p is 1..Iaddend.

.Iadd.57. A pharmaceutical composition, which comprises a compound as claimed in claim 46, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.58. An antipsychotic composition which comprises a compound as claimed in claim 46, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.59. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating effective amount of a compound as claimed in claim 46..Iaddend.

.Iadd.60. An analgesic composition which comprises a compound as claimed in claim 46, in an amount sufficient to produce a pain-relieving effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.61. A method of alleviating pain which comprises administering to a mammal a pain-relieving effective amount of a compound as claimed in claim 46..Iaddend.

.Iadd.62. The compound of claim 46, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts mineral acids, salts of monobasic carboxylic acids, salts of dibasic carboxylic acids, and salts of tribasic carboxylic acids..Iaddend.

.Iadd.63. The compound of claim 62, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts of hydrochloric acid, sulfuric acid, nitric acid, acetic is acid, propionic acid, maleic acid, fumaric acid, carboxysuccinic acid, and citric acid..Iaddend.

.Iadd.64. A compound of the formula ##STR00206## wherein X is --O--, --S--, --NH--, or ##STR00207## R.sub.2 is selected from the group consisting lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is as defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro or amino, when p is 1; Y is lower alkoxy, alkoxy hydroxy, or halogen p is 2 and X is --O--; (R.sub.1) is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1-C.sub.4 linear alkyl group, phenyl group or ##STR00208## wherein Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, or halogen; R.sub.20 is --(CH.sub.2).sub.n--where n is 2, 3, 4 or 5; R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl, thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; wherein alkyl is lower alkyl; aryl is phenyl or ##STR00209## wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, flourine, bromine, iodine, lower monoalkylamino, lower dialkylamino nitro, cyano, trifluoromethyl or trifluoromethoxy; heteroaryl is ##STR00210## wherein Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)-heteroaryl, wherein and heteroaryl are as defined above; and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1C.sub.4 alkoxy, or --COOR.sub.23 wherein R.sub.23 is H or C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, R.sub.1 is R.sub.20, R is H, and m=1; all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof..Iaddend.

.Iadd.65. A compound as claimed in claim 64, wherein X is --O--, --S--, or --NH--..Iaddend.

.Iadd.66. A compound as claimed in claim 64, wherein Y is hydrogen, chlorine, bromine, or fluorine..Iaddend.

.Iadd.67. A compound as claimed in claim 64, wherein n is 2, 3, or 4..Iaddend.

.Iadd.68. A compound and as claimed in claim 64, wherein n is 2, 3, or 4..Iaddend.

.Iadd.69. A compound as claimed in claim 64, wherein X is --S--..Iaddend.

.Iadd.70. A compound as claimed in claim 64, wherein X is --NH--..Iaddend.

.Iadd.71. A compound as claimed in claim 64, wherein X is --N(R.sub.2)..Iaddend.

.Iadd.72. A compound as claimed in claim 64, wherein X is --O--, --S--, or --NH--; Y is H, Cl, F, or --CF.sub.3; R is selected from the group consisting of hydrogen, C.sub.2-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, --OH, Cl, F, Br, I, C.sub.1-C.sub.3 monoalkylamino, acylamino, --NO.sub.3, --OCF.sub.3, and --CF.sub.3; and n is 2, 3, or 4..Iaddend.

.Iadd.73. A compound claimed in claim 72, wherein the substituent Y is in the 5- or 6-position..Iaddend.

.Iadd.74. A compound as claimed in claim 73, wherein m is 2..Iaddend.

.Iadd.75. A compound as claimed in claim 73, wherein n is 3..Iaddend.

.Iadd.76. A compound as claimed in claim 73, wherein p is 1..Iaddend.

.Iadd.77. A pharmaceutical composition, which comprises a compound as claimed in claim 64, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.78. An antipsychotic composition which comprises a compound as claimed in claim 64, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.79. A method of treating psychoses, which comprises a administering to a mammal a psychosis-treating effective amount of a compound as claimed in claim 64..Iaddend.

.Iadd.80. An analgesic composition which comprises a compound as claimed in claim 64, in an amount sufficient to produce a pain-relieving effect and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.81. A method of alleviating pain, which comprises administering a mammal a pain-relieving effective amount of a compound as claimed in claim 64..Iaddend.

.Iadd.82. The compound of claim 64, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts of mineral acids, salts of monobasic carboxylic acids, salts of dibasic carboxylic is acids, and salts of tribasic carboxylic acids..Iaddend.

.Iadd.83. The compound of claim 82, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts of hydrochloric acid, sulfuric acid, nitric acid, acetic acid, propionic acid, maleic acid, fumaric acid, carboxysuccinic acid, and citric acid..Iaddend.

.Iadd.84. A pharmaceutical composition, which comprises a compound of the formula ##STR00211## wherein X is --O--, --S--, --NH--, or ##STR00212## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10)cycloalkyl, aroyl,(C.sub.2-C.sub.11)alkanoyl, and phenylsulfonyl groups; aryl is defined hereinafter; p is 2; Y is hydrogen, lower alkyl hydroxy, chlorine, fluorine, bromine, iodine lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when is p is 2 and X is --O--; (R.sub.1) is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl, thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, dialkylaminocarbonyl formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; where alkyl is lower alkyl; aryl is phenyl or ##STR00213## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00214## where Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)-heteroaryl, where aryl and heteroaryl are as defined above; and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4, alkyl, chlorine, fluorine, bromine, iodine cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is C.sub.1-C.sub.4 alkyl; all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.85. A pharmaceutically composition, which comprises a compound of the formula ##STR00215## wherein X is --O--, --S--, --NH--, or ##STR00216## R.sub.3 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10)cycloalkyl, aroyl,(C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, iodine, lower alkoxy, trifluoromethyl, hydroxy, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when p is 2 and X is --O--; (R.sub.1) s R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1-C.sub.6 linear alkyl group phenyl group or ##STR00217## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, or halogen; R.sub.20 is --(CH.sub.2).sub.n--, where n is 2, 3, 4 or 5; R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2--, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2--, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl, thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; where alkyl is lower alkyl; aryl is phenyl or ##STR00218## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, flourine, bromine, iodine, lower monoalkylamino, lower dialkylamino nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00219## where Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)-heteroaryl, where and heteroaryl are as defined above; and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, R.sub.1 is R.sub.20, R is H, and m=1; all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.86. An antipsychotic composition, which comprises a compound of the formula ##STR00220## wherein X is --O--, --S--, --NH--, or ##STR00221## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl,(C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when p is 2 and X is --O--; (R.sub.1) is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, dialkylaminocarbonyl, formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, 13 C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; where alkyl is lower alkyl; aryl is phenyl or ##STR00222## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00223## where Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CH.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)--heteroaryl, where aryl and heteroaryl are as defined above; and m is 1, 2 or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is C.sub.1-C.sub.4 alkyl; all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.87. An antipsychotic composition, which comprises a compound of the formula ##STR00224## wherein X is --O--, --S--, --NH--, or ##STR00225## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10)cycloalkyl, aroyl,(C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when p is 2 and X is --O--; (R.sub.1) is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1-C.sub.4 linear alkyl group, phenyl group or ##STR00226## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, or halogen; R.sub.20 is --(CH.sub.2).sub.n--where n is 2, 3, 4 or 5; (R.sub.1) is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, dialkylaminocarbonyl, formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, 13 C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; where alkyl is lower alkyl; aryl is phenyl or ##STR00227## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00228## where Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)--heteroaryl, where aryl and heteroaryl are as defined above; and m is 1, 2 or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, R.sub.1 is R.sub.20, R is H, and m=1; all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.88. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating effective amount of a composition as claimed in claim 86..Iaddend.

.Iadd.89. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating effective amount of a composition as claimed in claim 87..Iaddend.

.Iadd.90. An analgesic composition, which comprises a compound of the formula ##STR00229## wherein X is --O--, --S--, --NH--, or ##STR00230## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10)cycloalkyl, aroyl,(C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when p is 2 and X is --O--; (R.sub.1) is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, dialkylaminocarbonyl, formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, 13 C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; where alkyl is lower alkyl; aryl is phenyl or ##STR00231## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00232## where Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--(C.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl..Iaddend.

.Iadd.91. An analgesic composition, which comprises a compound of the formula ##STR00233## wherein X is --O--, --S--, --NH--, or ##STR00234## R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10)cycloalkyl, aroyl,(C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1; Y is lower alkoxy, hydroxy, or halogen when p is 2 and X is --O--; (R.sub.1) is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1-C.sub.4 linear alkyl group, phenyl group or ##STR00235## where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, or halogen; R.sub.20 is --(CH.sub.2).sub.n--where n is 2, 3, 4 or 5; R.sub.21 is --CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--, --CH.sub.2--CH.dbd.CH--CH.sub.2--CH.sub.2, --CH.sub.2--CH.sub.2--CH.dbd.CH--CH.sub.2--, --CH.sub.2--C.dbd.C--CH.sub.2--CH.sub.2--, or --CH.sub.2--CH.sub.2--C.dbd.C--CH.sub.2, the --CH.dbd.CH-- bond being cis or trans; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl, --C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; where alkyl is lower alkyl; aryl is phenyl or ##STR00236## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, trifluoromethoxy; heteroaryl is ##STR00237## where Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or alkyl R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)--heteroaryl, where aryl and heteroaryl are as defined above; and m is 1, 2 or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, R.sub.1 is R.sub.20, R is H, and m=1; all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof, in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.92. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of a composition as claimed in claim 90..Iaddend.

.Iadd.93. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of a composition as claimed in claim 91..Iaddend.

.Iadd.94. A compound of the formula ##STR00238## wherein X is --O--, --S--, --NH--, or ##STR00239## R.sub.2 is selected from the group consisting lower alkyl, aryl lower alkyl, aryl, (C.sub.3-C.sub.10) cycloalkyl, aroyl, (C.sub.2-C.sub.11) alkanoyl, and phenylsulfonyl groups; aryl is as defined hereinafter; p is 1 or 2; Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro or amino, when p is 1; Y is lower alkoxy, alkoxy hydroxy, or halogen p is 2 and X is --O--; n is 2, 3, or 5; R is hydrogen, lower alkyl, lower alkoxy, hydroxyl, carboxyl, chlorine, fluorine, bromine, iodine, amino, lower mono or dialkylamino, nitro, lower alkyl, thio, trifluoromethoxy, cyano, acylamino, trifluoromethyl, trifluoroacetyl, aminocarbonyl, dialkylaminocarbonyl formyl, --C(.dbd.O)-alkyl, --C(.dbd.O)--O-alkyl, --C(.dbd.O)-aryl, --C(.dbd.O)-heteroaryl, --CH(OR.sub.7)-alkyl; --C(.dbd.W)-alkyl, --C(.dbd.W)-aryl, or --C(.dbd.W)-heteroaryl; alkyl is lower alkyl; aryl is phenyl or ##STR00240## where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, flourine, bromine, iodine, lower monoalkylamino, lower dialkylamino nitro, cyano, trifluoromethyl or trifluoromethoxy; heteroaryl is ##STR00241## Q.sub.3 is --O--, --S--, --NH--, or --CH.dbd.N--; W is CH.sub.2 or CHR.sub.8 or N--R.sub.9; R.sub.7 is hydrogen, lower alkyl, or lower alkyl--C(.dbd.O)--; R.sub.8 is lower alkyl; R.sub.9 is hydroxy, lower alkoxy, or --NHR.sub.10; and R.sub.10 is hydrogen, lower alkyl, C.sub.1-C.sub.3 acyl, aryl, --C(.dbd.O)-aryl, or --C(.dbd.O)-heteroaryl, where aryl and heteroaryl are as defined above; and m is 1, 2, or 3; with the exclusion of compounds wherein X is O or S, Y is hydrogen, and R is hydrogen, C.sub.1-C.sub.4 alkyl, chlorine, fluorine, bromine, iodine, cyano, C.sub.1-C.sub.4 alkoxy, or --COOR.sub.23 where R.sub.23 is C.sub.1-C.sub.4 alkyl; where R.sub.23 is C.sub.1-C.sub.4 alkyl; with the exclusion of compounds wherein X is --S--, R is H, and m=1; all geometric, optical and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof..Iaddend.

.Iadd.95. A compound as claimed in claim 94, wherein X is --O--, --S--, --NH..Iaddend.

.Iadd.96. A compound as claimed in claim 94, wherein Y is hydrogen, chlorine, bromine, or fluorine..Iaddend.

.Iadd.97. A compound as claimed in claim 94, wherein n is 2, 3, or 4..Iaddend.

.Iadd.98. A compound as claimed in claim 94, wherein X is --O--..Iaddend.

.Iadd.99. A compound as claimed in claim 94, wherein X is --S--..Iaddend.

.Iadd.100. A compound as claimed in claim 94, wherein X is --NH--..Iaddend.

.Iadd.101. A compound as claimed in claim 94, wherein X is.Iaddend. ##STR00242##

.Iadd.102. A compound as claimed in claim 94, wherein is --O--, --S--, or --NH--; Y is H, Cl, F, or --CF.sub.3; R is selected from the group consisting of hydrogen C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, --OH, Cl, F, Br, I, C.sub.1-C.sub.3 monoalkylamino, acylamino, --NO.sub.2, --OCF.sub.3, or --CF.sub.3; and n is 2, 3, or 4..Iaddend.

.Iadd.103. A compound as claimed in claim 102, wherein the substituent Y is in the 5- or 6-position..Iaddend.

.Iadd.104. A compound as claimed in claim 103, wherein m is 2..Iaddend.

.Iadd.105. A compound as claimed in claim 103, wherein n is 3..Iaddend.

.Iadd.106. A compound as claimed in claim 103, wherein p is 1..Iaddend.

.Iadd.107. A pharmaceutical composition, which comprises a compound as claimed in claim 94, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.108. An antipsychotic composition which comprises a compound as claimed in claim 94, in an amount sufficient to produce an antipsychotic effect, a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.109. A method of treating psychoses, which comprises ministering to a mammal a psychoses-treating amount of a compound as claimed in claim 94..Iaddend.

.Iadd.110. An analgesic composition which comprises a compound as claimed in claim 94, in an amount sufficient to produce a pain-relieving effect, and a pharmaceutically acceptable carrier therefor..Iaddend.

.Iadd.111. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of a compound as claimed in claim 94..Iaddend.

.Iadd.112. The compound of claim 94, wherein said pharmaceutically acceptable acid addition salt is selected from the group consisting of salts of acids, slats of monobasic carboxylic acids, salts of dibasic carboxylic acids, and salts of tribasic carboxylic acids..Iaddend.

.Iadd.113. The compound of claim 112, wherein said pharmaceutically acceptable acid addition salt is selected from the group of salts of hydrochloric acid, sulfuric acid, nitric acid, acetic acid propionic acid, maleic acid, fumaric acid, carboxysuccinic acid, and citric acid..Iaddend.
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